19492-99-0

Usage

Uses

Used in Organic Synthesis:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a building block for the synthesis of various organic compounds. Its unique structure and reactivity make it a versatile component in the creation of complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the development of new drugs. Its sulfur-containing heterocyclic structure and methoxy group provide specific properties that can be exploited for medicinal chemistry applications, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Research:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is utilized in chemical research for studying the properties and reactivity of benzo[b]thiophene derivatives. Its unique structure allows researchers to explore new reaction pathways and mechanisms, contributing to the advancement of organic chemistry.
Used in Material Science:
In material science, 5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER may be employed in the development of new materials with specific properties. Its sulfur-containing heterocyclic structure and methoxy group can influence the physical and chemical characteristics of materials, potentially leading to innovative applications in various industries.
Used in Agrochemical Industry:
5-METHOXY-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER can be used in the agrochemical industry as a precursor for the synthesis of pesticides or other agrochemicals. Its unique chemical properties may contribute to the development of more effective and environmentally friendly products for agricultural use.

InChI:InChI=1/C11H10O3S/c1-13-8-3-4-9-7(5-8)6-10(15-9)11(12)14-2/h3-6H,1-2H3

Upstream product

• 105728-90-3 2-fluoro-5-methoxybenzaldehyde 
• 2365-48-2 Methyl thioglycolate 
• 41280-81-3 methyl 3-chloro-5-methoxybenzo[b]thiophene-2-carboxylate 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 23046-02-8 5-(methoxy)-1-benzothiophene-2-carboxylic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1301265-10-0 2-gem-dibromovinyl-4-methoxylbenzothiol 
• 20532-30-3 5-methoxybenzothiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 

Downstream Products

• 41280-83-5 4-chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester 
• 23046-02-8 5-(methoxy)-1-benzothiophene-2-carboxylic acid 
• 13771-75-0 5-chloro-benzo(b)thiophene-2-carboxylic acid 
• 82788-15-6 5-hydroxybenzothiophene-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors

As a member of the signal transducer and activator of transcription (STAT) family, STAT3 plays a critical role in several biological pathways such as cell proliferation, migration, survival, and differentiation. Due to abnormal continuous activation in tumors, inhibition of STAT3 has emerged as an attractive approach for the treatment of various cancer cells. Herein, we report a series of novel STAT3 inhibitors based on benzo[b]thiophene 1,1-dioxide scaffold and evaluated their anticancer potency. Among them, compound 8b exhibited the best activity against cancer cells. Compound 8b induced apoptosis and blocked the cell cycle. Meanwhile, 8b reduced intracellular ROS content and caused the loss of mitochondrial membrane potential. Further research revealed that 8b significantly blocked STAT3 phosphorylation and STAT3-dependent dual-luciferase reporter gene experiments showed that compound 8b has a marked inhibition of STAT3-mediated Firefly luciferase activity. Molecular modeling studies revealed compound 8b occupied the pocket well with the SH2 domain in a favorable conformation.

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C?H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

Hydroxybenzothiophene ketones are efficient pre-mRNA splicing modulators due to dual inhibition of Dyrk1A and Clk1/4

Dysregulated usage of pre-mRNA splicing sites contributes to the progression of cancer, neurodegenerative diseases, and viral infections. Serine/arginine-rich (SR) proteins play major roles in the splice site recognition and are largely regulated by phosp

HETEROCYCLIC DERIVATIVES AND USE THEREOF

A heterocyclic derivative represented by formula (I), or a pharmaceutically acceptable salt or a stereoisomer thereof, which has an inhibitory effect on the activation of STAT3 protein, and is useful for the prevention or treatment of diseases associated with the activation of STAT3 protein.

Palladium-catalyzed domino C-S coupling/carbonylation reactions: An efficient synthesis of 2-carbonylbenzo[ b ]thiophene derivatives

A facile and selective palladium-catalyzed domino procedure has been developed for the preparation of 2-carbonylbenzo[b]thiophene derivatives from 2-gem-dihalovinylthiophenols. This protocol involves intramolecular C-S coupling/intermolecular carbonylatio

NOVEL INHIBITORS OF BETA-LACTAMASE

This invention provides novel β-lactamase inhibitors of the aryl- and heteroarylsulfonamidomethylphosphonate monoester class having nitrogen-based cations or quarternary ammonium groups. The compounds inhibit three classes of β-lactamases and synergize the antibacterial effects of β-lactam antibiotics (e.g., imipenem and ceftazidime) against those micro-organisms normally resistant to the β-lactam antibiotics as a result of the presence of the β-lactamases. Formula (I) or pharmaceutically acceptable salt thereof.

CHEMILUMINESCENT COMPOSITIONS, METHODS, ASSAYS AND KITS FOR OXIDATIVE ENZYMES

Chemiluminescent compositions, methods, assays and kits for oxidative enzymes are described. Further disclosed are dioxetane compounds of the form: 0-0 ΛR R R T (i) where R can independently be any branched alkyl or cycloalkyl group which provides stabili

BENZOFURAN AND BENZOTHIOPHENE-2-CARBOXYLIC ACID AMIDE DERIVATIVES

The present invention relates to compounds of formula I wherein X, A and R1 to R4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

Axially chiral 3,3′-bi(1-benzothiophene)-2,2′-dicarboxylic acid and its derivatives

Ullmann dimerization of substituted methyl 3-X-1-benzothiophene-2-carboxylates 1-7 (X = Cl, Br) gave rise to the corresponding dimeric 3,3′-bi(1-benzothiophene) esters 8-13. Resolution of the title acid 20 by fractional crystallization of its mono- and bisquininium salt afforded pure (R)- and (S)-enantiomers, the optical purity and absolute configuration of which was confirmed by CD spectrometry and by X-ray crystallography. Ullmann dimerization of chiral oxazolines 23 and 24 derived from 2 proceeded without any diastereodifferentiation. Reduction of (R)- and (S)-20 afforded the corresponding (R)- and (S)-diols 29, which served as chiral ligands in a model enantioselective reduction of acetophenone. (R)- and (S)-1-phenylethan-1-ol were formed in 28 and 29% e.e., respectively.